Synthesis of Illudinine from Dimedone
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- 作者：Alec E. Morrison ; Tung T. Hoang ; Mélodie Birepinte ; Gregory B. Dudley
- 刊名：Organic Letters
- 出版年：2017
- 出版时间：February 17, 2017
- 年：2017
- 卷：19
- 期：4
- 页码：858-861
- 全文大小：344K
- ISSN：1523-7052
文摘
A total synthesis of the illudalane sesquiterpene illudinine was realized in eight steps and 14% overall yield from commercially available dimedone. The approach features tandem fragmentation/Knoevenagel-type condensation and microwave-assisted oxidative cycloisomerization to establish the isoquinoline core. Completion of the synthesis involves a recently reported cascade SNAr/Lossen rearrangement on a densely functionalized aryl bromide and an optimized procedure for O-methylation of 8-hydroxyisoquinolines. The oxidative cycloisomerization proceeds by way of a novel inverse-demand intramolecular dehydro-Diels–Alder cycloaddition, which has a potentially broader appeal for preparing substituted isoquinolines.